Tert-butyl ethyl (5-nitropyrazin-2-yl)propanedioate → Ethyl 2-(5-nitropyrazin-2-yl)acetate
Reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[N:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
A mixture of tert-butyl ethyl (5-nitropyrazine-2-yl)propanedioate (10.7 g, 34.4 mmol) in 30 mL of TFA and 30 mL DCM was stirred at 35° C. for 3 hours before concentrated to dryness. The residue was dissolved in 200 mL of EtOAc and washed with water (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated to afford ethyl (5-nitropyrazine-2-yl)acetate.
Workup
- concentrationbefore concentrated to dryness
- dissolutionThe residue was dissolved in 200 mL of EtOAc
- washwashed with water (25 mL) and brine (25 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a50718e839304bf3b8fdbe20102f51d7
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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